Shagenes A and B, new tricyclic sesquiterpenes produced by an undescribed Antarctic octocoral

Org Lett. 2014 May 16;16(10):2630-3. doi: 10.1021/ol500792x. Epub 2014 Apr 29.

Abstract

The isolation and characterization of two new tricyclic sesquiterpenoids, shagenes A (1) and B (2) are presented. These compounds were isolated from an undescribed soft coral collected from the Scotia Arc in the Southern Ocean. One- and two-dimensional NMR spectroscopy and mass spectrometry provided the data necessary to characterize the compounds and their relative stereochemical configurations. Exploration of the bioactivity of shagenes A and B found 1 active against the visceral leishmaniasis causing parasite, Leishmania donovani, with no cytotoxicity against the mammalian host.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antarctic Regions
  • Anthozoa / chemistry*
  • Leishmania donovani / drug effects*
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Parasitic Sensitivity Tests
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Sesquiterpenes
  • shagene A
  • shagene B